Tandem silylformylation-crotylsilylation/Tamao oxidation of internal alkynes: a remarkable example of generating complexity from simplicity.

ABSTRACT: The rhodium-catalyzed tandem silylformylation-crotylsilylation reaction has been extended to include internal alkynes. Tamao oxidation of the initial product leads to the production of a substituted enol, which undergoes highly diastereoselective tautomerization. The resulting one-pot procedure fashions three new stereocenters, a ketone, and a terminal alkene from a butenyl group, a propynyl group, a silyl hydride, H2O2, and CO.

SUBMITTER: Spletstoser JT 

PROVIDER: S-EPMC2628290 | biostudies-literature | 2008 Dec

REPOSITORIES: biostudies-literature